Water → HCID 21835877, compound

HRID 1739601Notes

Reaction equation

HRID 1739601 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)=[CH2:2].[Br-].[C:17]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CCC=C)C=CC=C[CH:18]=1.[CH3:40][C:41](C)([O-])C.[K+].O>C1COCC1>[CH:1](=[C:3]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:14][CH2:13][CH:12]([CH:40]=[CH2:41])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1)[CH2:2][CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962WaterHCID 1097132416958-42-2HCID 15430757HCID 15430757, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21835877HCID 21835877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

20.6 g of 4'-vinylbicyclohexyl-4-one and 39.7 g of triphenyl(3-butenyl)phosphonium bromide in 250 ml of THF were cooled to -10° C. under nitrogen with stirring. A solution of 11.44 g of potassium tert-butoxide in 150 ml of THF was then added dropwise at -10° C. with stirring, and the mixture was then stirred at RT for a further 2 hours. The yellow suspension was cooled to 10° C., and 500 ml of water were added. The organic phase was separated off, and the aqueous phase was extracted once with 100 ml of methyl tert-butyl ether. Combined organic extracts were washed once with 100 ml of water, dried using sodium sulfate, filtered and evaporated to give a residue, giving 4'-but-3-enylidene-4-vinylbicyclohexyl.

Workup

  1. stirringwith stirring
  2. stirringthe mixture was then stirred at RT for a further 2 hours
  3. customThe organic phase was separated off
  4. extractionthe aqueous phase was extracted once with 100 ml of methyl tert-butyl ether
  5. washCombined organic extracts were washed once with 100 ml of water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customto give a residue

Sources & evidence

ORD record
ord-d9429738e9a1446db6d53784bd27e029
Source dataset
uspto-grants-1999_10
Patent number
US05968410

Reaction notes

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